I have about $500 to play with and want to buy some new gear. Not sure if I should focus on getting my lighting or buying a new lens. Right now I have my kit lens that came with the T3i. A canon EF 50mm 1.8 and a Canon EFS 55 to 250mm 4.0 to 5.6.

As far as lighting goes all I have is a YongNuo YN-468 II E-TTL that I mount to the camera.

I shoot outside 90% of the time. So I'm wondering how important more lighting really is. I know it's a broad question, but I want to make sure I get whatever might help me improve the quality of my work.

George Ruge wrote: Lighting-wise, the first thing to do is get the light away from the camera. A decent set of radio triggers, a light stand and a brollybox would be a good start.

Amen brother.
As far as how important lighting is.... if you want that perfect sunset, a nice blue sky with white clouds, or those serious dramatic clouds, chances are, you're gonna end up metering too dark on your subject. It can be done without lights, it's done all the time without them. But if you can, why not? Meter on the whitest cloud in a blue sky about a stop or two to the left, and fill in on the subject. Or, on a completely overcast day, meter those clouds two or more stops dark, to really enhance them, but put them in the background where they need to be. Light, gotta have it.

It's 2 am, and I have been drinking, so take what I say with a grain of salt until tomorrow, when I can go into further detail.

$500 can go a long way.

The 468II is a quite good on camera flash for events and whatnot... but as mentioned above, off camera is where it's at. I've been using the RF-603 radio triggers for a while now with zero problems... great budget gear.

I have always suggested the YN460II for off camera use. It's fantastic for a dumb flash.

If you need more power outdoors, toss three in an umbrella with a cheap bracket like this $12 thing (works well enough for me) and you've got some decent power for $150ish (and when moving indoors, you have THREE lights.)

A LOT depends on what you actually want/need. Given your lens setup, I would recommend a Tamron 17-50 2.8 (will take up $250-300 or so of your budget) and then another flash or two if you need more power, and some nice modifiers.

George Ruge wrote: Lighting-wise, the first thing to do is get the light away from the camera. A decent set of radio triggers, a light stand and a brollybox would be a good start.

^^This!^^
Normally I would suggest new glass because that's how I feed MY addiction...but honestly, Controlling Light is what we do as Photographers.
That skill is what allows us to turn an ordinary snapshot into a true Photograph! Looking at your portfolio I see some excellently framed images that simply seem a little flat to me.
Getting a light setup such as the one suggested above would allow you to begin to sculpt the light and make *it* do as *you* like, rather than for you to be at the mercy of the available bounced light and shade at your particular location.

ShotbyRon wrote: I have about $500 to play with and want to buy some new gear. Not sure if I should focus on getting my lighting or buying a new lens.

Question 1: what do you want to accomplish that your current gear doesn't let you do?

Question 2: why doesn't it let you do so?

Without an answer to both of those, advice is kind of risky. Two photographers with identical gear and nominally similar subject can have wildly different goals, and each might well 'need' very different things: lighting tools (what kind?), education (in what?), lenses (which?), etc.

I'm not critiquing here but the only way to improve your skills is through education. I'd take at least some of that money and invest into things like Kelby Training or Lynda.com THEN you will know what items you will need to do the kinds of shots you want to take.

If you like available light, why buy a strobe? Sure it can be added but only if that's the look you are going for. You can do amazing things with just a reflector, a gobo, a diffuser, etc. without adding any artificial lights.

Thanks for the help! I'm going to buy a few pieces of lighting, but invest the rest of the money (and then some) into renting a studio and going to a group event. It will give me practice working with experienced models, lighting (indoors and out) etc. And I'll go from there.

Question 1: what do you want to accomplish that your current gear doesn't let you do?

Question 2: why doesn't it let you do so?

Without an answer to both of those, advice is kind of risky. Two photographers with identical gear and nominally similar subject can have wildly different goals, and each might well 'need' very different things: lighting tools (what kind?), education (in what?), lenses (which?), etc.

I think if the OP knew specifically they wouldnt be posing the open-ended question. Its a tough process coming up with goals and self evaluating your work to get there. Sometimes its an easy choice, like it was years ago when all kit lenses were shite and the only reliable triggers were PWs. The answer was "both but only one was affordable". Sometimes its not so clear and we need more experience to figure it out. Now kit lenses are fine, they just don't have 2.8 or 1.7 apertures to get a certain effect some of us like/want.

OTOH I'd be willing to bet that most of us have come to the point where have put in the the thought, know our goals, know several things could help our work and are trying to prioritize. And then there is 'like' and 'gearlust' that come into play. If I had $$$ to play today I might be asking the question "better lightstands or better booms?" Someone else might be asking "seamless or cloth?" I know we often ask
"what are you trying to do?" and on the surface it seems the right question. But sometimes it just makes things more confusing for the OP.

Now that I've wasted page space, I'm going to go with George's suggestion. getting the flash off camera, simply because it's an inexpensive option that can be done for way less than 500$. That way, if the OP finds they still need better glass they have a head start on saving for it. If better glass doesn't turn out to help them, it will be more daunting thinking about saving up for the off-camera kit.

I think I'm going to just say the hell with it and get both. What is a good portrait lens for around $700 or less? Some people told me to get fixed for portrait, but I'm not a fan. Are they really better though?

ShotbyRon wrote: I think I'm going to just say the hell with it and get both. What is a good portrait lens for around $700 or less? Some people told me to get fixed for portrait, but I'm not a fan. Are they really better though?

I like prime lenses I used to shoot them, but, for my work primes were not practical. They were to heavy bulky and made me carry extra camera bodies. My work through is location driven, be it photojournalism, event photography, sports, editorial or commercial. Because of that I carry my gear with me. I as far portraits I do a lot of EP work. I can also have a complete portable studio that I can set up in under 30 min.

Because of these needs I carry 3 basic zoom lenses, Prime Lens and one 1.4x Teleconvertor.

I think it really comes down to the type of work you do, and what you can afford. Based off of what you have posted so far I would lean towards a zoom. Mainly it will give you more flexibility and coverage for the dollar. If were talking more money and more lenses then a couple of primes makes more sense to me.

ShotbyRon wrote: I think I'm going to just say the hell with it and get both. What is a good portrait lens for around $700 or less? Some people told me to get fixed for portrait, but I'm not a fan. Are they really better though?

I love my EF 100mm f/2.0 for portraits. Others like the 85 1.8 or the 2.8 version of the 100mm. - all under your budget (half)

ShotbyRon wrote: I think I'm going to just say the hell with it and get both. What is a good portrait lens for around $700 or less? Some people told me to get fixed for portrait, but I'm not a fan. Are they really better though?

It would depend what type of lens you like. Personally I'm in favor with the prime lenses and my suggestion would be to sell the 55-250mm for whatever you can get and go with either an 85mm 1.8 or the 100mm 2.0; as I see you shoot mostly portraits. Yes I would get a decent radio trigger to get your flash off camera and buy a lightstand with some modifier. Cheapest option for that would be an umbrella. Get an white umbrella and a silver one.

I've seen used 85mm anywhere from 250-300$
Lightstand roughly 50-75$
Umbrellas roughtly 25$
Radio triggers... do your research on that... honestly for outdoor shooting, whenever I travel, I just use the cowboy studio trigger. $25 and they have last me for 2 years so far..

I am going to toss out the idea that you go to a camera store and buy a book on photography in the style you like. Learn what you need to make those kinds of pictures and then make equipment decisions.